Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-10-03
1997-09-16
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514374, 548131, 548143, 548235, C07D27106, A01N 4376
Patent
active
056681607
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB94/00502 filed Mar. 15, 1994.
The present invention relates to fungicidal oxazolyl and oxadiazolyl derivatives, to processes for preparing them, to fungicidal compositions comprising them and to methods of using them to combat fungi, especially fungal infections of plants.
Fungicidal alkoxyacrylate and oxyiminoacetate compounds are known. (See, for example, EP-A-178826, EP-A-242081, EP-A-253213, EP-A-370629, EP-A-382375 and WO 92/18487.) The present invention is distinguished from these known compounds by replacing the alkoxyacrylate or oxyiminoacetate group with the group Q--C.dbd.Z.OCH.sub.3 (wherein Q and Z are as defined below).
According to the present invention there is provided a compound of formula (I), wherein Q is oxazol-2-yl, 1,3,4-oxadiazol-2-yl, 1,2,4-oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl; Z is CH or N; A is hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, cyano, nitro or trifluoromethyl; X is halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl optionally substituted cycloalkyl OR.sup.1, SR.sup.1, SOR.sup.1, SO.sub.2 R.sup.1, COR.sup.1, CO.sub.2 R.sup.1, NR.sup.1 R.sup.2 or CONR.sup.1 R.sup.2 ; R.sup.1 and R.sup.2 and are, independently, hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl.
Optionally substituted alkyl includes alkyl substituted by one or more halogen atoms or by a hydroxy, alkoxy, haloalkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, cycloalkyl, arylthio or heteroarylthio group, or, when the optionally substituted alkyl group is a value of X, it can also be optionally substituted by an R.sup.1' R.sup.2' C.dbd.NO group (wherein R.sup.1' and R.sup.2' independently, hydrogen, optionally substituted alkyl (for example, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted arylalkyl, optionally substituted heteroarylalkyl, optionally substituted heteroaryloxyalkyl or optionally substituted aryloxyalkyl), optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, nitro, halogen, NR'R" (wherein R' and R" are as defined below) or cyano, or R.sup.1' and R.sup.2' join to form a carbocyclic or heterocyclic ring system (suitably a C.sub.5-10 aliphatic, aromatic or mixed aliphatic/aromatic carbocyclic ring system, for example cyclopentyl, cyclohexyl or cyclohexadienonyl and such groups carrying a fused benzene ring and/or substituents such as methyl; or it may be a 5- to 10-membered heterocyclic ring system, for example tetrahydropyranyl)).
Optionally substituted alkenyl and optionally substituted alkynyl include alkenyl and alkynyl groups optionally substituted with halogen, aryl, aryloxy, arylthio, heteroaryl, heteroaryloxy or heteroarylthio.
Because the double bond of the Q--C.dbd.Z.OCH.sub.3 group is unsymmetrically substituted, the compounds of the invention may be obtained in the form of mixtures of (E)- and (Z)-geometric isomers. However, these mixtures can be separated into individual isomers, and this invention embraces such isomers and mixtures thereof in all proportions including those which consist substantially of the (Z)-isomer and those which consist substantially of the (E)-isomer.
In one aspect the present invention provides a compound of formula (Ie), wherein A, Q and Z are as defined above; W is O, OCH.sub.2, CH.sub.2 O, S, SCH.sub.2, CH.sub.2 S, CH.sub.2, CH.sub.2 CH.sub.2, CH.dbd.CH, C.ident.C, R.sup.3 C.dbd.NOCH.sub.2 (thus forming, with Y, the group YR.sup.3 C.dbd.NOCH.sub.2 or NR.sup.4 ; Y is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted arylalkyl or heteroarylalkyl; R.sup.
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Clough John Martin
Crowley Patrick Jelf
Delaney John Stephen
Gerstl Robert
Snyder Joseph R.
Thomson Marian T.
Zeneca Limited
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